Jack Dorsey grew up in St. Louis fascinated by maps, dispatch systems, and how cities functioned. He taught himself programming as a teenager, hacking into dispatch software. By age 15, he’d built open-source dispatch logistics software still used today.
He enrolled at NYU but dropped out after two years. In 2000, he moved to California and pitched his idea for a real-time status update platform—essentially Twitter—to multiple companies. Everyone rejected it. The idea seemed pointless. Who cares about 140-character updates?
For years, Jack worked odd jobs, sketching ideas, refining his vision. Then, in March 2006, he sent the first tweet: ‘just setting up my twttr.’ Twitter launched publicly in July 2006. Growth was slow. Critics mocked it as useless. The challenge: how do you convince people they need something they don’t understand?
The Turning Point
Twitter exploded during SXSW 2007 when attendees used it to coordinate meetups. Tweets increased 300%. Twitter became the platform for real-time global conversation—Arab Spring, Black Lives Matter, presidential elections. It changed journalism, activism, and public discourse forever.
But Jack wasn’t satisfied. In 2009, he started Square, a payment processing company. The challenge: credit card processing was expensive, complex, and inaccessible to small businesses. Square’s solution: a tiny dongle that plugged into smartphones, turning any phone into a payment terminal.
Banks laughed. Regulators pushed back. Jack built anyway. By 2015, Square IPO’d at $2.9 billion. Today it’s worth over $40 billion.
The Strategy
Simplicity: Twitter’s 140-character limit forced clarity. Square’s dongle was so simple anyone could use it. Complexity is the enemy of adoption.
Solve Real Problems: Twitter solved real-time communication. Square solved payment accessibility. Both addressed genuine pain points.
Run Two Companies Simultaneously: Jack served as CEO of both Twitter and Square—something Silicon Valley said was impossible. He proved focus isn’t about limiting scope; it’s about ruthless prioritization.
Accept Criticism, Stay Focused:Twitter was mocked as frivolous. Square was called a toy. Jack ignored critics and built.
The Results
Twitter: 450+ million active users, cultural force that changed politics, journalism, and activism.
Square: Processes $200+ billion annually, serves millions of small businesses, valued at $40+ billion.
Jack Dorsey’s net worth: $5+ billion. He built two industry-defining companies simultaneously—a feat almost nobody has replicated.
